Resist composition, method of forming resist pattern, polymeric compound, and compound

Abstract

A resist composition which can form a very fine resist pattern with excellent lithography properties, a new polymeric compound useful for the resist composition, and a compound useful as a monomer for the polymeric compound. The resist composition contains a polymeric compound containing a structural unit (a0) represented by general formula (a0) shown below. In the formula (a0), A is an anion represented by the general formula (1) or (2).

What is claimed is 
     
       1. A resist composition which exhibits changed solubility in an alkali developing solution upon exposure, comprising:
 a polymeric compound (A) having a structural unit (a0) represented by general formula (a0) shown below: 
 
       
         
           
           
               
               
           
         
       
       wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; R 1  represents a divalent aromatic cyclic group; each of R 2  and R 3  independently represents an aryl group with or without a substituent, an alkyl group with or without a substituent or an alkenyl group with or without a substituent, wherein R 2  and R 3  may be mutually bonded to form a ring with the sulfur atom; L 1  represents a single bond or a divalent linking group; and A represents an anion represented by general formula (11a), (11b), (11c), (11e), (11f), (12a), (12b), (12c), (12d) or (2) shown below: 
       
         
           
           
               
               
           
         
       
       wherein in formula (11a), X 10  represents an —S(═O) 2 — containing cyclic group, p represents an integer of 1 to 3, and Q 12  represents a single bond or an alkylene group;
 in formula (11b), X 10  represents a hydrocarbon group of 3 to 30 carbon atoms with or without a substituent, p represents an integer of 1 to 3, and Q 13  represents an alkylene group; 
 in formula (11c), p represents an integer of 1 to 3, X 10 ′ represents a fluorinated aryl group with or without a substituent, and Q 14  represents a single bond or an alkylene group; 
 in formula 11e), X 10  represents a hydrocarbon group of 3 to 30 carbon atoms with or without a substituent, p represents an integer of 1 to 3, Q 16  represents an alkylene group, and Q 17  represents a methylene group; 
 in formula (11f), X 10  represents a hydrocarbon group of 3 to 30 carbon atoms with or without a substituent, p represents an integer of 1 to 3, and Q 13 ′ represents an alkylene group 
 in the formulae (12a), (12b), (12c) and (12d), R 7 ″ represents a substituent, w01 represents an integer of 0 to 7, w02 represents an integer of 0 to 5, w03 represents an integer of 0 to 15, each of v01 to v04 independently represents an integer of 0 to 5, and pp represents an integer of 1 to 3; and in formula (2), R 6  represents an alkyl group with or without a substituent or a fluorinated alkyl group with or without a substituent; L 3  represents a single bond or a divalent linking group; Y 10  represents a —CO—; and R 7  represents a hydrocarbon group with or without a substituent. 
 
     
     
       2. The resist composition according to  claim 1 , wherein the polymeric compound (A) comprises an acid dissociable, dissolution inhibiting group, and exhibits increased solubility in an alkali developing solution by the action of acid. 
     
     
       3. The resist composition according to  claim 1 , wherein the polymeric compound (A) further comprises a structural unit (a1) derived from an acrylate ester containing an acid dissociable, dissolution inhibiting group. 
     
     
       4. The resist composition according to  claim 3 , wherein the polymeric compound (A) further comprises a structural unit (a2) which is at least one structural unit selected from the group consisting of a structural unit derived from an acrylate ester containing a —SO 2 — containing cyclic group and a structural unit derived from an acrylate ester containing a lactone-containing cyclic group. 
     
     
       5. The resist composition according to  claim 3 , wherein the polymeric compound (A) further comprises a structural unit (a3) derived from an acrylate ester containing a polar group-containing aliphatic hydrocarbon group. 
     
     
       6. The resist composition according to  claim 1 , further comprising an acid-generator component (B) that generates acid upon exposure, exclusive of the polymeric compound (A). 
     
     
       7. The resist composition according to  claim 6 , wherein the acid-generator component (B) is an onium salt acid generator containing an anion moiety represented by general formula (1′) or (2′) shown below:
   R 5′ -L 2′ -R 4′ —SO 3   −   (1′)
 
   R 7′ -L 3′ -Y 10′ —N − —SO 2 —R 6′   (2′)
 
 
       wherein in formula (1′), R 4 ′ represents an alkylene group of 1 to 4 carbon atoms with or without a substituent or a fluorinated alkylene group of 1 to 4 carbon atoms with or without a substituent; L 2 ′ represents a single bond or a divalent linking group; and R 5 ′ represents a hydrocarbon group of 3 to 30 carbon atoms with or without a substituent; and in formula (2′), R 6 ′ represents an alkyl group with or without a substituent or a fluorinated alkyl group with or without a substituent; L 3 ′ represents a single bond or a divalent linking group; Y10′ represents a —SO 2 —or a —CO—; and R 7 ′ represents a hydrocarbon group with or without a substituent. 
     
     
       8. A method of forming a resist pattern, comprising:
 forming a resist film on a substrate using the resist composition of  claim 1 ; 
 exposing the resist film; and 
 alkali-developing the resist film to form a resist pattern. 
 
     
     
       9. A polymeric compound comprising a structural unit (a0) represented by general formula (a0) shown below: 
       
         
           
           
               
               
           
         
       
       wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; R 1  represents a divalent aromatic cyclic group; each of R 2  and R 3  independently represents an aryl group with or without a substituent, an alkyl group with or without a substituent or an alkenyl group with or without a substituent, wherein R 2  and R 3  may be mutually bonded to form a ring with the sulfur atom; L 1  represents a single bond or a divalent linking group; and A represents an anion represented by general formula (11a), (11b ), (11c), (11e), (11f), (12a), (12b), (12c), (12d) or (2) shown below: 
       
         
           
           
               
               
           
         
       
       wherein in formula (11a), X 10  represents an —S(═O) 2 — containing cyclic group, p represents an integer of 1 to 3, and Q 12  represents a single bond or an alkylene group;
 in formula (11b), represents a hydrocarbon group of 3 to 30 carbon atoms with or without a substituent, p represents an integer of 1 to 3, and Q 13  represents an alkylene group; 
 in formula (11c), p represents an integer of 1 to 3, X 10 ′ represents a fluorinated aryl group with or without a substituent, and Q 14  represents a single bond or an alkylene group; 
 in formula (11e), X 10  represents a hydrocarbon group of 3 to 30 carbon atoms with or without a substituent, p represents an integer of 1 to 3,Q 16  represents an alkylene group, and Q 17  represents a methylene group; 
 in formula (11f), X   represents a hydrocarbon group of 3 to 30 carbon atoms with or without a substituent, p represents an integer of 1 to 3,and Q 13 ′ represents an alkylene group 
 in the formulae (12a), (12b), (12c) and (12d), R 7 ″ represents a substituent, w01 represents an integer of 0 to 7, w02 represents an integer of 0 to 5, w03 represents an integer of 0 to 15, each of v01 to v04 independently represents an integer of 0 to 5, and pp represents an integer of 1 to 3; and in formula (2), R 6  represents an alkyl group with or without a substituent or a fluorinated alkyl group with or without a substituent; L 3  represents a single bond or a divalent linking group; Y 10  represents a —CO—; and R 7  represents a hydrocarbon group with or without a substituent. 
 
     
     
       10. The polymeric compound according to  claim 9 , which comprises an acid dissociable, dissolution inhibiting group, and exhibits increased solubility in an alkali developing solution by the action of acid. 
     
     
       11. The polymeric compound according to  claim 10 , which further comprises a structural unit (al) derived from an acrylate ester containing an acid dissociable, dissolution inhibiting group. 
     
     
       12. The polymeric compound according to  claim 11 , which further comprises a structural unit (a2) which is at least one structural unit selected from the group consisting of a structural unit derived from an acrylate ester containing a —SO 2 — containing cyclic group and a structural unit derived from an acrylate ester containing a lactone-containing cyclic group. 
     
     
       13. The polymeric compound according to  claim 11 , which further comprises a structural unit (a3) derived from an acrylate ester containing a polar group-containing aliphatic hydrocarbon group. 
     
     
       14. A compound represented by general formula (I) shown below: 
       
         
           
           
               
               
           
         
       
       wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; R 1  represents a divalent aromatic cyclic group; each of R 2  and R 3  independently represents an aryl group with or without a substituent, an alkyl group with or without a substituent or an alkenyl group with or without a substituent, wherein R 2  and R 3  may be mutually bonded to form a ring with the sulfur atom; L 1  represents a single bond or a divalent linking group; and A represents an anion represented by general formula (11a), (11b), (11c), (11e), (11f), (12a), (12b), (12c), (12d) or (2) shown below: 
       
         
           
           
               
               
           
         
       
       wherein in formula (11a), X 10  represents an —S(═O) 2 — containing cyclic group, p represents an integer of 1 to 3,and Q 12  represents a single bond or an alkylene group;
 in formula (11b), X 10  represents a hydrocarbon group of 3 to 30 carbon atoms with or without a substituent, p represents an integer of 1 to 3,and Q 13  represents an alkylene group; 
 in formula (11c), p represents an integer of 1 to 3, X 10 ′ represents a fluorinated aryl group with or without a substituent, and Q 14  represents a single bond or an alkylene group; 
 in formula (11e), X 10  represents a hydrocarbon group of 3 to 30 carbon atoms with or without a substituent, p represents an integer of 1 to 3, Q 16  represents an alkylene group, and Q 17  represents a methylene group; 
 in formula (11f), X 10  represents a hydrocarbon group of 3 to 30 carbon atoms with or without a substituent, p represents an integer of 1 to 3,and Q 13 ′ represents an alkylene group 
 in the formulae (12a), (12b), (12c) and (12d), R 7 ″ represents a substituent, w01 represents an integer of 0 to 7, w02 represents an integer of 0 to 5, w03 represents an integer of 0 to 15, each of v01 to v04 independently represents an integer of 0 to 5, and pp represents an integer of 1 to 3; and in formula (2), R 6  represents an alkyl group with or without a substituent or a fluorinated alkyl group with or without a substituent; L 3  represents a single bond or a divalent linking group; Y 10  represents a —CO—; and R 7  represents a hydrocarbon group with or without a substituent.